References

Total Synthesis of (±)-Maoecrystal V cites an improved Simmons-Smith reaction reported by Denis, Girard, and Conia (1972) using a Zn/Ag couple instead of a Zn/Cu couple. This was the basis for the reaction conditions chosen for the synthesis of molecule 43. The citation is below.

 

 

 

Denis, J. M.; Girard, C.; Conia, J. M. Synthesis 1972, 549-551.

 

Papers which also cited Denis, Girard, and Conia (1972):

1) In 2013, Cheng, Huang, and Shi described an efficient method to cyclopropanate alkenes with a catalytic amound of trichloroacetic acid (CCl₃CO₂H) and 1,2-dimethoxyethane. They reported that a variety of olefins could be cyclopropanated in a 71-99% yield with this method, which includes the use of a Zn/Ag couple to create the organozinc carbenoid.

 

 

 

 

Cheng, D.; Huang, D.; Shi, Y. Org. Biomol. Chem. 2013, 11, 5588-5591.

 

2) In 2009, Shi et al. described a reaction in which vinylidenecyclopropane, a cyclopropene attached to a diene via two successive double bonds, was cyclopropanated with the improved Simmon-Smith reaction cited above. This resulted in compounds in varying degrees of cyclopropanation, shown below.

 

 

Shi, M.; Shao, L. X.; Lu, J. M.; Wei, Y.; Mizuno, K.; Maeda, H. Chem. Rev. 2010, 110, 5883-5913.